NPASS Compound

Structure

NPC473279 OpenBabel07101719252D 33 38 0 0 1 0 0 0 0 0999 V2000 7.1038 0.6853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5686 2.3326 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3198 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1285 1.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1528 0.3763 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1225 2.2044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1006 1.9965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7624 0.5102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3607 1.3544 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4533 1.4612 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.4752 1.6691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.4096 1.0454 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7405 0.3023 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 8 9 1 0 0 0 0 8 23 1 0 0 0 0 9 24 1 0 0 0 0 10 14 1 0 0 0 0 10 21 1 0 0 0 0 11 13 1 0 0 0 0 11 22 1 0 0 0 0 12 15 1 0 0 0 0 12 25 1 0 0 0 0 13 28 1 0 0 0 0 14 29 1 0 0 0 0 15 30 1 0 0 0 0 16 17 1 0 0 0 0 16 27 1 0 0 0 0 18 21 1 0 0 0 0 18 33 1 0 0 0 0 19 30 1 0 0 0 0 19 31 1 0 0 0 0 20 29 1 0 0 0 0 21 22 1 0 0 0 0 22 27 1 6 0 0 0 23 26 1 0 0 0 0 23 30 1 6 0 0 0 24 28 1 1 0 0 0 24 31 1 0 0 0 0 25 26 1 0 0 0 0 25 32 1 6 0 0 0 27 28 1 6 0 0 0 28 6 1 1 0 0 0 29 7 1 1 0 0 0 29 33 1 0 0 0 0 30 31 1 1 0 0 0 31 17 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	456.4
Volume:	510.974
LogP:	6.973
LogD:	5.085
LogS:	-6.292
# Rotatable Bonds:	2
TPSA:	29.46
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.463
Synthetic Accessibility Score:	5.705
Fsp3:	1.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.134
MDCK Permeability:	1.9297604012535885e-05
Pgp-inhibitor:	0.027
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.89
30% Bioavailability (F30%):	0.967

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.088
Plasma Protein Binding (PPB):	96.10900115966797%
Volume Distribution (VD):	1.385
Pgp-substrate:	2.3807692527770996%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.328
CYP2C19-inhibitor:	0.074
CYP2C19-substrate:	0.961
CYP2C9-inhibitor:	0.14
CYP2C9-substrate:	0.109
CYP2D6-inhibitor:	0.088
CYP2D6-substrate:	0.657
CYP3A4-inhibitor:	0.734
CYP3A4-substrate:	0.703

ADMET: Excretion

Clearance (CL):	6.649
Half-life (T1/2):	0.074

ADMET: Toxicity

hERG Blockers:	0.859
Human Hepatotoxicity (H-HT):	0.286
Drug-inuced Liver Injury (DILI):	0.192
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.199
Maximum Recommended Daily Dose:	0.91
Skin Sensitization:	0.942
Carcinogencity:	0.074
Eye Corrosion:	0.618
Eye Irritation:	0.289
Respiratory Toxicity:	0.954

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC473279

Natural Product ID:	NPC473279
*Common Name:**	Berenjenol
IUPAC Name:	n.a.
Synonyms:	berenjenol
Standard InCHIKey:	QGUCSIMOQIAADS-HEHMHTDASA-N
Standard InCHI:	InChI=1S/C31H52O2/c1-20(2)29(7)14-10-21(18-33-29)22-11-13-28(6)24-9-8-23-26(3,4)25(32)12-15-30(23)19-31(24,30)17-16-27(22,28)5/h20-25,32H,8-19H2,1-7H3/t21?,22-,23+,24+,25+,27-,28+,29-,30-,31+/m1/s1
SMILES:	CC([C@@]1(C)CCC(CO1)[C@H]1CC[C@@]2([C@]1(C)CC[C@@]13[C@H]2CC[C@@H]2[C@]3(C1)CC[C@@H](C2(C)C)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL390981
PubChem CID:	16681372
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO33511	oxandra cf. xylopioides	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17402783]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	44.0	%	PMID[485300]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	64.0	%	PMID[485300]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	51.0	%	PMID[485300]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC473279 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	417
0.1-0.2	4815
0.2-0.3	17590
0.3-0.4	8218
0.4-0.5	4613
0.5-0.6	4450
0.6-0.7	1966
0.7-0.8	512
0.8-0.85	75
0.85-0.9	24
0.9-0.95	16
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9552	High Similarity	NPC282454
0.9412	High Similarity	NPC100586
0.9412	High Similarity	NPC109457
0.9412	High Similarity	NPC195530
0.9412	High Similarity	NPC157422
0.9143	High Similarity	NPC477508
0.9118	High Similarity	NPC299948
0.9118	High Similarity	NPC470830
0.9118	High Similarity	NPC241085
0.9104	High Similarity	NPC48079
0.9104	High Similarity	NPC473230
0.9104	High Similarity	NPC475884
0.9091	High Similarity	NPC474380
0.9091	High Similarity	NPC41577
0.9091	High Similarity	NPC473276
0.9	High Similarity	NPC473238
0.9	High Similarity	NPC472341
0.8971	High Similarity	NPC472741
0.8955	High Similarity	NPC142712
0.8939	High Similarity	NPC69149
0.8857	High Similarity	NPC8004
0.8857	High Similarity	NPC131506
0.8857	High Similarity	NPC157777
0.8857	High Similarity	NPC127283
0.8841	High Similarity	NPC129829
0.8841	High Similarity	NPC254037
0.8788	High Similarity	NPC114891
0.8714	High Similarity	NPC231945
0.8714	High Similarity	NPC192192
0.8649	High Similarity	NPC471769
0.8636	High Similarity	NPC71460
0.8636	High Similarity	NPC218585
0.8636	High Similarity	NPC148174
0.863	High Similarity	NPC470145
0.8592	High Similarity	NPC187471
0.8592	High Similarity	NPC1340
0.8592	High Similarity	NPC252182
0.8592	High Similarity	NPC470071
0.8592	High Similarity	NPC127094
0.8571	High Similarity	NPC107919
0.8571	High Similarity	NPC66407
0.8514	High Similarity	NPC476233
0.8493	Intermediate Similarity	NPC231680
0.8493	Intermediate Similarity	NPC91387
0.8493	Intermediate Similarity	NPC270306
0.8406	Intermediate Similarity	NPC44122
0.8382	Intermediate Similarity	NPC167995
0.8382	Intermediate Similarity	NPC281540
0.8382	Intermediate Similarity	NPC159654
0.8382	Intermediate Similarity	NPC118937
0.8358	Intermediate Similarity	NPC95804
0.8358	Intermediate Similarity	NPC185547
0.8356	Intermediate Similarity	NPC478130
0.8333	Intermediate Similarity	NPC95958
0.831	Intermediate Similarity	NPC477820
0.8289	Intermediate Similarity	NPC220379
0.8286	Intermediate Similarity	NPC63190
0.8267	Intermediate Similarity	NPC475031
0.8267	Intermediate Similarity	NPC474574
0.8267	Intermediate Similarity	NPC64081
0.8267	Intermediate Similarity	NPC11907
0.8267	Intermediate Similarity	NPC133596
0.8261	Intermediate Similarity	NPC260116
0.8261	Intermediate Similarity	NPC80463
0.8243	Intermediate Similarity	NPC70982
0.8243	Intermediate Similarity	NPC230704
0.8243	Intermediate Similarity	NPC273366
0.8243	Intermediate Similarity	NPC186851
0.8228	Intermediate Similarity	NPC474996
0.8219	Intermediate Similarity	NPC253805
0.8219	Intermediate Similarity	NPC153719
0.8205	Intermediate Similarity	NPC475388
0.8194	Intermediate Similarity	NPC251201
0.8194	Intermediate Similarity	NPC63588
0.8194	Intermediate Similarity	NPC232925
0.8182	Intermediate Similarity	NPC476735
0.8182	Intermediate Similarity	NPC16449
0.8158	Intermediate Similarity	NPC147993
0.8158	Intermediate Similarity	NPC472342
0.8108	Intermediate Similarity	NPC49168
0.8108	Intermediate Similarity	NPC254509
0.8108	Intermediate Similarity	NPC192501
0.8108	Intermediate Similarity	NPC272359
0.8108	Intermediate Similarity	NPC10476
0.8108	Intermediate Similarity	NPC196358
0.8108	Intermediate Similarity	NPC304499
0.8108	Intermediate Similarity	NPC228994
0.8108	Intermediate Similarity	NPC145552
0.8108	Intermediate Similarity	NPC5046
0.8082	Intermediate Similarity	NPC478103
0.8077	Intermediate Similarity	NPC73515
0.8052	Intermediate Similarity	NPC287452
0.8052	Intermediate Similarity	NPC81074
0.8052	Intermediate Similarity	NPC477282
0.803	Intermediate Similarity	NPC135438
0.8026	Intermediate Similarity	NPC23884
0.8026	Intermediate Similarity	NPC212453
0.8026	Intermediate Similarity	NPC257191
0.8026	Intermediate Similarity	NPC331618
0.8	Intermediate Similarity	NPC158208
0.8	Intermediate Similarity	NPC243027
0.8	Intermediate Similarity	NPC174964
0.8	Intermediate Similarity	NPC97534
0.8	Intermediate Similarity	NPC3403
0.8	Intermediate Similarity	NPC200243
0.8	Intermediate Similarity	NPC196136
0.8	Intermediate Similarity	NPC190827
0.8	Intermediate Similarity	NPC178383
0.8	Intermediate Similarity	NPC243469
0.8	Intermediate Similarity	NPC212879
0.8	Intermediate Similarity	NPC231256
0.8	Intermediate Similarity	NPC195155
0.8	Intermediate Similarity	NPC475943
0.8	Intermediate Similarity	NPC104387
0.8	Intermediate Similarity	NPC240235
0.8	Intermediate Similarity	NPC317242
0.7975	Intermediate Similarity	NPC296734
0.7973	Intermediate Similarity	NPC195489
0.7973	Intermediate Similarity	NPC470610
0.7973	Intermediate Similarity	NPC232112
0.7971	Intermediate Similarity	NPC292419
0.7971	Intermediate Similarity	NPC290791
0.7952	Intermediate Similarity	NPC228059
0.7949	Intermediate Similarity	NPC248944
0.7949	Intermediate Similarity	NPC7479
0.7949	Intermediate Similarity	NPC257296
0.7922	Intermediate Similarity	NPC471045
0.7922	Intermediate Similarity	NPC42853
0.7917	Intermediate Similarity	NPC475893
0.7917	Intermediate Similarity	NPC474756
0.791	Intermediate Similarity	NPC162685
0.7901	Intermediate Similarity	NPC290612
0.7895	Intermediate Similarity	NPC86305
0.7895	Intermediate Similarity	NPC163597
0.7895	Intermediate Similarity	NPC93662
0.7895	Intermediate Similarity	NPC14112
0.7895	Intermediate Similarity	NPC278091
0.7895	Intermediate Similarity	NPC91573
0.7895	Intermediate Similarity	NPC78067
0.7895	Intermediate Similarity	NPC475742
0.7895	Intermediate Similarity	NPC5767
0.7875	Intermediate Similarity	NPC472744
0.7867	Intermediate Similarity	NPC62657
0.7867	Intermediate Similarity	NPC192638
0.7867	Intermediate Similarity	NPC48795
0.7867	Intermediate Similarity	NPC25511
0.7848	Intermediate Similarity	NPC12933
0.7848	Intermediate Similarity	NPC58631
0.7838	Intermediate Similarity	NPC58057
0.7838	Intermediate Similarity	NPC111234
0.7838	Intermediate Similarity	NPC151018
0.7838	Intermediate Similarity	NPC320549
0.7838	Intermediate Similarity	NPC156277
0.7821	Intermediate Similarity	NPC476176
0.7821	Intermediate Similarity	NPC49599
0.7821	Intermediate Similarity	NPC155924
0.7821	Intermediate Similarity	NPC49627
0.7808	Intermediate Similarity	NPC99264
0.7792	Intermediate Similarity	NPC302578
0.7792	Intermediate Similarity	NPC119355
0.7792	Intermediate Similarity	NPC171658
0.7792	Intermediate Similarity	NPC221420
0.7792	Intermediate Similarity	NPC248830
0.7792	Intermediate Similarity	NPC185915
0.7792	Intermediate Similarity	NPC105208
0.7792	Intermediate Similarity	NPC143133
0.7792	Intermediate Similarity	NPC212241
0.7792	Intermediate Similarity	NPC202540
0.7792	Intermediate Similarity	NPC128951
0.7792	Intermediate Similarity	NPC477227
0.7792	Intermediate Similarity	NPC192046
0.7792	Intermediate Similarity	NPC298168
0.7778	Intermediate Similarity	NPC86238
0.7778	Intermediate Similarity	NPC204233
0.7763	Intermediate Similarity	NPC212733
0.7763	Intermediate Similarity	NPC185536
0.7761	Intermediate Similarity	NPC236588
0.775	Intermediate Similarity	NPC60018
0.775	Intermediate Similarity	NPC61107
0.775	Intermediate Similarity	NPC289486
0.775	Intermediate Similarity	NPC154043
0.775	Intermediate Similarity	NPC202688
0.7746	Intermediate Similarity	NPC472946
0.7722	Intermediate Similarity	NPC261616
0.7722	Intermediate Similarity	NPC206735
0.7714	Intermediate Similarity	NPC236099
0.7714	Intermediate Similarity	NPC209686
0.7714	Intermediate Similarity	NPC249078
0.7711	Intermediate Similarity	NPC43912
0.7711	Intermediate Similarity	NPC140446
0.7703	Intermediate Similarity	NPC45296
0.7692	Intermediate Similarity	NPC18857
0.7692	Intermediate Similarity	NPC31828
0.7692	Intermediate Similarity	NPC301707
0.7692	Intermediate Similarity	NPC477577
0.7692	Intermediate Similarity	NPC285761
0.7692	Intermediate Similarity	NPC85346
0.7692	Intermediate Similarity	NPC302041
0.7692	Intermediate Similarity	NPC102708
0.7692	Intermediate Similarity	NPC67657

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC473279 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	425
0.1-0.2	4438
0.2-0.3	3122
0.3-0.4	689
0.4-0.5	179
0.5-0.6	234
0.6-0.7	38
0.7-0.8	24
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8571	High Similarity	NPD4267	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD4787	Phase 1
0.7949	Intermediate Similarity	NPD6928	Phase 2
0.7838	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD6117	Approved
0.7632	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD6116	Phase 1
0.75	Intermediate Similarity	NPD7525	Registered
0.7468	Intermediate Similarity	NPD6115	Approved
0.7468	Intermediate Similarity	NPD6114	Approved
0.7468	Intermediate Similarity	NPD6697	Approved
0.7468	Intermediate Similarity	NPD6118	Approved
0.7432	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD5360	Phase 3
0.7308	Intermediate Similarity	NPD3703	Phase 2
0.7237	Intermediate Similarity	NPD4244	Approved
0.7237	Intermediate Similarity	NPD4245	Approved
0.7237	Intermediate Similarity	NPD4789	Approved
0.7105	Intermediate Similarity	NPD3698	Phase 2
0.7089	Intermediate Similarity	NPD3702	Approved
0.7059	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD7645	Phase 2
0.6923	Remote Similarity	NPD4758	Discontinued
0.6889	Remote Similarity	NPD8171	Discontinued
0.6875	Remote Similarity	NPD7339	Approved
0.6875	Remote Similarity	NPD6942	Approved
0.6829	Remote Similarity	NPD3671	Phase 1
0.6778	Remote Similarity	NPD8034	Phase 2
0.6778	Remote Similarity	NPD8035	Phase 2
0.6753	Remote Similarity	NPD6705	Phase 1
0.6709	Remote Similarity	NPD5777	Approved
0.6667	Remote Similarity	NPD371	Approved
0.6667	Remote Similarity	NPD4748	Discontinued
0.6627	Remote Similarity	NPD5364	Discontinued
0.6585	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD7991	Discontinued
0.6543	Remote Similarity	NPD6926	Approved
0.6543	Remote Similarity	NPD6924	Approved
0.6515	Remote Similarity	NPD385	Approved
0.6515	Remote Similarity	NPD384	Approved
0.65	Remote Similarity	NPD6081	Approved
0.6494	Remote Similarity	NPD4224	Phase 2
0.6484	Remote Similarity	NPD6700	Approved
0.6484	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD4788	Approved
0.6413	Remote Similarity	NPD6703	Approved
0.6413	Remote Similarity	NPD6702	Approved
0.6404	Remote Similarity	NPD8308	Discontinued
0.6386	Remote Similarity	NPD6933	Approved
0.6374	Remote Similarity	NPD5328	Approved
0.6364	Remote Similarity	NPD4786	Approved
0.63	Remote Similarity	NPD6920	Discontinued
0.6296	Remote Similarity	NPD4243	Approved
0.625	Remote Similarity	NPD6695	Phase 3
0.6237	Remote Similarity	NPD6079	Approved
0.6222	Remote Similarity	NPD3618	Phase 1
0.62	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD7638	Approved
0.618	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.617	Remote Similarity	NPD4202	Approved
0.6154	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD1811	Approved
0.6145	Remote Similarity	NPD1810	Approved
0.6145	Remote Similarity	NPD4784	Approved
0.6145	Remote Similarity	NPD4785	Approved
0.6136	Remote Similarity	NPD3667	Approved
0.6122	Remote Similarity	NPD7640	Approved
0.6122	Remote Similarity	NPD7639	Approved
0.6098	Remote Similarity	NPD7151	Approved
0.6098	Remote Similarity	NPD7152	Approved
0.6098	Remote Similarity	NPD7150	Approved
0.6092	Remote Similarity	NPD7509	Discontinued
0.6092	Remote Similarity	NPD6931	Approved
0.6092	Remote Similarity	NPD6930	Phase 2
0.6082	Remote Similarity	NPD7919	Phase 3
0.6082	Remote Similarity	NPD7920	Phase 3
0.6061	Remote Similarity	NPD4159	Approved
0.6049	Remote Similarity	NPD6923	Approved
0.6049	Remote Similarity	NPD6922	Approved
0.602	Remote Similarity	NPD8088	Phase 1
0.6019	Remote Similarity	NPD6415	Discontinued
0.6	Remote Similarity	NPD7632	Discontinued
0.6	Remote Similarity	NPD6399	Phase 3
0.598	Remote Similarity	NPD7128	Approved
0.598	Remote Similarity	NPD6402	Approved
0.598	Remote Similarity	NPD5739	Approved
0.598	Remote Similarity	NPD6675	Approved
0.5978	Remote Similarity	NPD7750	Discontinued
0.5978	Remote Similarity	NPD7524	Approved
0.5977	Remote Similarity	NPD6929	Approved
0.5976	Remote Similarity	NPD7144	Approved
0.5976	Remote Similarity	NPD7143	Approved
0.596	Remote Similarity	NPD8418	Phase 2
0.5938	Remote Similarity	NPD7748	Approved
0.593	Remote Similarity	NPD6932	Approved
0.5922	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD4755	Approved
0.5895	Remote Similarity	NPD7515	Phase 2
0.5882	Remote Similarity	NPD4190	Phase 3
0.5882	Remote Similarity	NPD5275	Approved
0.5882	Remote Similarity	NPD386	Approved
0.5882	Remote Similarity	NPD388	Approved
0.5865	Remote Similarity	NPD6899	Approved
0.5865	Remote Similarity	NPD7320	Approved
0.5865	Remote Similarity	NPD6881	Approved
0.5843	Remote Similarity	NPD6902	Approved
0.5824	Remote Similarity	NPD3665	Phase 1
0.5824	Remote Similarity	NPD3133	Approved
0.5824	Remote Similarity	NPD3666	Approved
0.5821	Remote Similarity	NPD367	Approved
0.5818	Remote Similarity	NPD7328	Approved
0.5818	Remote Similarity	NPD7327	Approved
0.5816	Remote Similarity	NPD4697	Phase 3
0.5816	Remote Similarity	NPD5221	Approved
0.5816	Remote Similarity	NPD5222	Approved
0.5816	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.581	Remote Similarity	NPD6372	Approved
0.581	Remote Similarity	NPD6373	Approved
0.58	Remote Similarity	NPD4700	Approved
0.58	Remote Similarity	NPD4696	Approved
0.58	Remote Similarity	NPD5285	Approved
0.58	Remote Similarity	NPD5286	Approved
0.5795	Remote Similarity	NPD6683	Phase 2
0.5795	Remote Similarity	NPD4195	Approved
0.5783	Remote Similarity	NPD2687	Approved
0.5783	Remote Similarity	NPD2686	Approved
0.5783	Remote Similarity	NPD2254	Approved
0.5769	Remote Similarity	NPD5697	Approved
0.5769	Remote Similarity	NPD5701	Approved
0.5766	Remote Similarity	NPD7516	Approved
0.5761	Remote Similarity	NPD6893	Approved
0.5758	Remote Similarity	NPD6084	Phase 2
0.5758	Remote Similarity	NPD5173	Approved
0.5758	Remote Similarity	NPD7902	Approved
0.5758	Remote Similarity	NPD6083	Phase 2
0.5755	Remote Similarity	NPD7102	Approved
0.5755	Remote Similarity	NPD6883	Approved
0.5755	Remote Similarity	NPD7290	Approved
0.5747	Remote Similarity	NPD6925	Approved
0.5747	Remote Similarity	NPD5776	Phase 2
0.5745	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD5223	Approved
0.5741	Remote Similarity	NPD8133	Approved
0.573	Remote Similarity	NPD7514	Phase 3
0.5729	Remote Similarity	NPD7087	Discontinued
0.5727	Remote Similarity	NPD7115	Discovery
0.5714	Remote Similarity	NPD8377	Approved
0.5714	Remote Similarity	NPD6011	Approved
0.5714	Remote Similarity	NPD8294	Approved
0.5714	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5701	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5701	Remote Similarity	NPD6847	Approved
0.5701	Remote Similarity	NPD6649	Approved
0.5701	Remote Similarity	NPD8130	Phase 1
0.5701	Remote Similarity	NPD6617	Approved
0.5701	Remote Similarity	NPD6650	Approved
0.5701	Remote Similarity	NPD6869	Approved
0.5686	Remote Similarity	NPD5226	Approved
0.5686	Remote Similarity	NPD5211	Phase 2
0.5686	Remote Similarity	NPD4633	Approved
0.5686	Remote Similarity	NPD5225	Approved
0.5686	Remote Similarity	NPD5224	Approved
0.5684	Remote Similarity	NPD6051	Approved
0.5684	Remote Similarity	NPD4753	Phase 2
0.5682	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5682	Remote Similarity	NPD7145	Approved
0.5664	Remote Similarity	NPD8378	Approved
0.5664	Remote Similarity	NPD8033	Approved
0.5664	Remote Similarity	NPD8380	Approved
0.5664	Remote Similarity	NPD8296	Approved
0.5664	Remote Similarity	NPD8379	Approved
0.5664	Remote Similarity	NPD8335	Approved
0.566	Remote Similarity	NPD6013	Approved
0.566	Remote Similarity	NPD6012	Approved
0.566	Remote Similarity	NPD6014	Approved
0.5648	Remote Similarity	NPD6882	Approved
0.5648	Remote Similarity	NPD8297	Approved
0.5636	Remote Similarity	NPD6940	Discontinued
0.5631	Remote Similarity	NPD4754	Approved
0.5631	Remote Similarity	NPD5175	Approved
0.5631	Remote Similarity	NPD5174	Approved
0.5604	Remote Similarity	NPD4223	Phase 3
0.5604	Remote Similarity	NPD4221	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data